Beckmann rearrangement of nucleoside-5-oxime

摘要

The oxime of 5-formyl-2′-deoxyuridine (I) can be dehydrated by acetic anhydride to give 5-cyano-2′-deoxyuridine (II). In the HBr/acetic acid/acetic anhydride mixture I becomes rearranged to 5-N-acetamido-2-deoxyuridine (III).The pathway of this unexpected reaction is investigated.